1. Field of the Invention
This invention relates to novel N-acylamino acid compounds and a method for the production thereof. More particularly, it relates to novel compounds produced by acylating histidine and peptide containing histidine with a long-chain fatty acid and possessed of many functionalities such as antioxidizing power, emulsifying power, antibacterial power, chelating power, ultraviolet absorbing power, and humidity-retaining power and a method for the production thereof.
2. Description of the Prior Art
In recent years, the postulate that active oxygen induces various oxidizing reactions and constitutes itself a notorious cause for various diseases such as senility, arteriosclerosis, and cancers has come to be advocated and studies devoted to the development of an antioxidant capable of inhibiting the oxidzing reactions have been gaining in impetus. In the food industry, for example, such synthetic antioxidants as BHT (3,5-t-butyl-4-hydroxy toluene) and BHA (2,(3)-6-butyl-4-hydroxy anisole) are used as inexpensive and highly efficient antioxidants.
Since the detection of the carcinogenic action in these compounds, particularly in BHA, was reported, doubts have come to be cast on the safety of the compounds. Tocopherols which are used as naturally occurring antioxidants, in spite of their outstanding antioxidizing power, betray sparing solubility in water and liability to promote oxidation at a high concentration and, therefore, find only restricted utility in cosmetic preparations and foodstuffs. Other polyphenols which are possessed of an antioxidizing power fit only restricted applications on account of their weak point of exhibiting high solubility in water and sparing solubility in oil.
An object of this invention, therefore, is to provide novel acyl compounds and a method for the production thereof.
Another object of this invention is to provide novel compounds possessed of functionalities such as antioxidizing power, emulsifying power, antibacterial power, chelating power, ultraviolet absorbing power, and humidity-retaining power and a method for the production thereof.
These objects are accomplished by an N-acylamino acid compound represented by the general formula (1): EQU R--CO--(NH--X--CO).sub.n --OR.sup.1 ( 1)
wherein (NH--X--CO) is an amino acid residue, X in (NH--X--CO) is variable with the kind of an amino acid to be used, R--CO is a saturated or unsaturated fatty acid residue having 6 to 24 carbon atoms, R.sup.1 is hydrogen atom, sodium atom, potassium atom, or methyl group, and n is an integer in the range of from 1 to 3, indicating that at least one histidine is contained as a component amino acid.
These objects are further accomplished by a method for the production of an N-acylamino acid compound represented by the general formula (1): EQU R--CO--(NH--X--CO).sub.n --OR.sup.1 ( 1)
wherein (NH--X--CO) is an amino acid residue, X in (NH--X--CO) is variable with the kind of an amino acid to be used, R--CO is a saturated or unsaturated fatty acid residue having 6 to 24 carbon atoms, R.sup.1 is hydrogen atom, sodium atom, potassium atom, or methyl group, and n is an integer in the range of from 1 to 3, indicating that at least one histidine is contained as a component amino acid, characterized by causing an N-hydroxysuccinimide ester represented by the general formula (2): ##STR1## wherein R--CO has the same meaning as defined above, to react with an amino acid or a peptide represented by the general formula (3): EQU H--(NH--X--CO).sub.n --OR.sup.1 ( 3)
wherein (NH--X--CO), X, R--CO, R.sup.1, and n have the same meanings as defined above, indicating that at least one histidine is contained as a component amino acid.
The objects are also accomplished by an antioxidant having as an active component thereof an N-acylamino acid compound represented by the general formula (1): EQU R--CO--(NH--X--CO).sub.n --OR.sup.1 ( 1)
wherein (NH--X--CO) is an amino acid residue, X in (NH--X--CO) is variable with the kind of an amino acid to be used, R--CO is a saturated or unsaturated fatty acid residue having 6 to 24 carbon atoms, R.sup.1 is hydrogen atom, sodium atom, potassium atom, or methyl group, and n is an integer in the range of from 1 to 3, indicating that at least one histidine is contained as a component amino acid.
The objects are further accomplished by an emulsifier having as an active component thereof an N-acylamino acid compound represented by the general formula (1): EQU R--CO--(NH--X--CO).sub.n --OR.sup.1 ( 1)
wherein (NH--X--CO) is an amino acid residue, X in (NH--X--CO) is variable with the kind of an amino acid to be used, R--CO stands for a saturated or unsaturated fatty acid residue having 6 to 24 carbon atoms, R.sup.1 is hydrogen atom, sodium atom, potassium atom, or methyl group, and n is an integer in the range of from 1 to 3, indicating that at least one histidine is contained as a component amino acid.
The N-acylamino acid compounds and the method for production thereof according to this invention are as described above and, therefore, are novel to the art. These compounds are novel antioxidants which exhibit an antioxidizing power in polar and nonpolar solvents. Further, these compounds are possessed of a very high emulsifying power and antibacterial power, chelating power, ultraviolet absorbing power, and warmth-retaining power as well and, therefore, are highly useful as raw materials for cosmetic goods, foodstuffs, medicines, etc.